The 40 Best Questions to Ask

in an Interview — How to Go
Deeper Than “What’s the
Culture Like?”
When it comes to interviewing advice, there’s plenty to go around
for hiring managers. We’ve certainly covered our fair share here on
the Review — none more popular than last year's 40 Favorite
Interview Questions from Some of the Sharpest Folks We Know.

Since we published this guide, it’s racked up hundreds of thousands

of views and received tons of wonderfully-kind feedback, turning
into something of a staple for interviewers prepping to dig in with a
candidate. We were thrilled to see that getting folks to share their
best interview questions — and crucially, why they ask it and what
makes for a good answer — seemed to strike a chord. It confirmed
our hunch that despite the wealth of content around crafting
the right questions, there’s still a hunger for these resources to keep
your hiring skills top-notch.
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And there’s an appetite to match it on the other side of the table, of
course. As a candidate, prepping for a job interview can feel like a
job that’s never fully done. From shaping up your resume and
settling on the key stories to highlight from your career path, to
researching the company and stalking the interview panel on
LinkedIn, there’s a daunting pile of prep work to tackle — and an
insatiable need for advice to help get you through it.
Today we’re focusing on those moments when the interviewer turns
to candidates and asks the inevitable, “Do you have any questions
for me?” at the end of the interview. It's critical to come up with a
slate of good questions to ask that uncover vital information about
the job opportunity — and simultaneously serve up another chance
to highlight your strengths as the ideal candidate.

But too often, interviewees fail to stand out here. There’s an easy
temptation to focus on other aspects of prep and thus fall back on
the most common interview questions over and over again — think
“Why did you join this company?” or “What does a typical day
look like here?” At best, these may elicit an interesting anecdote
from your interviewer. At worst, you’ve wasted precious minutes
just dipping a toe into the pool, instead of probing the most critical
depths of this new role and your potential employer.

Since we’re always on the hunt for tactics and advice that can fill in
existing gaps, we’ve spent the past month reaching out to some of
the most thoughtful founders and startup leaders in our network for
their take on this question:

What should candidates ask in interviews?

We were especially focused on unearthing the best questions that

are not often raised, whether they were queries these leaders
themselves have previously posed before joining a company, or
ones they wish more candidates would put to them when they’ve
got their hiring hats on. A few contributors will be familiar from
previous Review articles, but most are new faces, eager to share
their insights.

We were already big admirers of this group, but what we got in

return blew us away: A wealth of favorite interview questions to
keep in your back pocket, all that dig much deeper than the ones
like “What’s the culture like?” that just barely scratch the surface.
Their responses span across all sorts of different categories, from
the company’s future and the team’s biggest challenges, to
professional development opportunities and what your day-to-day
responsibilities will really look like. While some of the questions
are geared towards sussing out valuable information — whether
that’s red flags or indicators that it’s your dream job — others are
oriented towards reinforcing your thoughtfulness to the interview
panel. Not every question will be relevant to you or your role, but
we promise you’ll find at least a few that you haven’t thought of
before.
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But while there’s plenty of variety, there’s also a clear common
thread. Regardless of role, industry, or seniority, nearly all of
leaders we polled were singing the same tune: Interviewees are on
the receiving end of the questions, and thus have a very limited
window to pose their own questions at the end of an interview.
Before taking your seat across from the hiring manager, priortize
around what’s most important in your new job: Company growth,
personal role and responsibility, a great team and manager. Every
single question you ask should clearly map back to those priorities
— and pack a punch.

Matt Wallaert, one of our favorites here on the Review and the

former Chief Behavioral Officer at Clover Health, put an even finer
point on this. “Before I narrow down my list of questions, I always
ask myself, ‘Would I change my decision about working here based
on the answer?’ If the answer is no, then there is no point in asking
the question.”

When jotting down the questions for

your interview panel, focus on your
 deal breakers: What would make you
walk away?
Anna Binder, Head of People Operations at Asana, takes a
systematic approach here — narrowing down her list of possibly
dozens of “nice-to-haves” to just the top five must-have criteria.
“You need a proactive, intentional and mindful approach to
managing your career. A lot of folks get caught up in a mindset that
I liken to teenage dating — you get so excited that someone likes
you, that you lose sight of whether or not you even like them
back. Putting those five must-haves on paper puts you in the
driver’s seat so you can be the CEO of your own career.”

With that framing in mind, we’ve broken this mega-list of smart

questions down to eight targeted categories, based on what you
might care about most in your job search. Click the links below to
navigate to each section:

 Company growth and priorities: What’s on the horizon for the

company, and what are the biggest blockers to reaching that
summit?
 Culture and values: How does the company want to conduct
its work?
 Diversity, equality and inclusion : What tangible steps is the
company taking to put DEI efforts front-and-center?
 Employee experience: What factors determine whether or not
someone is successful at growing within the company?
 Founder fit: For those interviewing at early-stage startups,
how do you assess whether the founding team is well-equipped for
the bumpy road that lies ahead?
 Manager compatibility: Will you and your manager work
harmoniously, and will they be someone who gently nudges you to
be better?
 Role and responsibilities: Does the role adequately fulfill the
next steps you’re looking to accomplish in your career?
 Team impact and dynamics: How does the team function as a
unit to drive meaningful change for the company and its customers?
We hope this serves as a rich starting block for pulling together a
roster of questions that crystalizes whether the role and company in
front of you is the perfect fit. Let’s dive in.

INTERVIEW QUESTIONS ON COMPANY GROWTH

AND PRIORITIES

1. What’s the biggest existential threat to this business?

What are the things that keep you up at night?

This straight-shooting question comes courtesy of Shreyas

Subramaniam, Director of Product Management at Airbase, and
should be near the top of the list for any job seeker. Regardless of
your role or main priorities for your next gig, sketching out a more
nuanced understanding of the business (aside from what you can
dig up poking around on Google) is key to grasping what lies ahead
if you join. A variation of this question popped up numerous times
in our conversations (which clued us into just how valuable of a
query it is), so we’ll also share a few alternative ways to approach
it:
Jake Fuentes, Co-founder and CEO, Cascade
Kevin Caldwell, Co-founder and CEO of Ossium Health, likes to
bifurcate the question this way: What's the biggest external risk to
the company? What is the biggest Internal risk? Which worries you
more?

Jake Fuentes, Co-founder and CEO at Cascade, approaches it a bit

differently: If the company failed in 18 months, what’s the likely
reason why? Now let’s say it’s a breakout success, what was the
critical thing it did right? “I find this two-pronged approach reveals
the real risk factors and opportunities for the business and —
perhaps more importantly — how clear leadership is on those
areas,” he says.

2. What are the most recent examples of things the

company has tried and failed at?

With this question, Jeanne DeWitt Grosser, Head of Americas

Revenue and Growth at Stripe, isn’t necessarily zeroing in
on what the actual failure was — any startup vet knows that plenty
of coal will turn up in your search for that diamond. Instead, mine
for why it was a failure and how your potential employer responded.
Is the interviewer honest in their answer, or trying to paint too rosy
of a picture? Was the company able to pivot and right the ship? The
response should also clearly articulate what the learnings were and
how they trickled down across the company.

Sitting on the opposite end of the interview table, Max Mullen, Co-

founder of Instacart, has been asked a related question: What were
the single best and worst days/weeks in Instacart's journey? “As an
interviewer you're often answering the same questions over and
over — a hard question like this one gives you pause and actually
makes you think of the answer on the fly,” he says.

When the candidate has the courage to

ask a question that might challenge the
interviewer, that’s a positive signal. I
want them to ask the hard questions
once they’re inside the company, too.
3. What are some of the key financial metrics that the
company optimizes for?
“I don't think enough candidates ask about the business itself,
regardless of the product,” says David Nunez, Head of
Documentation at Stripe. “This question gives great insight into the
health of the company, what they prioritize, and also reflects well
on you as the candidate — you’re signaling that you really want to
do your homework,” he says.

4. What are the top three customers that you’ve won, and
the top three customers that you’ve lost?

We love that this question from Max Branzburg (VP of Product

at Coinbase) requires a more specific answer than overly-sanitized
marketing speak: “You get a real sense of how they're doing in the
market, what's working well — and what's not,” he says. Key here
is to also dig in with your follow-up questions: What are they doing
to replicate their biggest wins, and what are the most valuable
takeaways from the losses?
Kaye Mao, Interaction Designer, Google Health

5. Which companies does the leadership admire and hope

to emulate? Why?

Kaye Mao, Interaction Designer at Google Health, loves this

question she first heard from design vet Julie Zhuo (whose inside
look at Facebook’s practices for hiring designers is still a Review
favorite). In our view, it goes back to the heart of your interview
process as a candidate — what’s most important in your next role?
Answers here should indicate the company’s most powerful driving
force, whether that be culture, hypergrowth, or delivering customer
value. How closely does the company’s motivation align with your
own?

6. What area of the business would you say this company

is behind on, given its stage?

Cristina Cordova, Head of Platform and Partnerships at Notion,

likes to lean on this question for getting a sense of the company’s
bigger picture — and how that might impact your own role. “This
question can often highlight functions that are not established and
areas where you have to fill in cross-functionally that might surprise
you,” she says.

Another way of approaching this question, also from Max Mullen

of Instacart, is: If you had a magic wand, what would you change
about the company?

INTERVIEW QUESTIONS ON CULTURE AND

VALUES

7. What’s something that would only happen here but

wouldn’t at other organizations?

This one comes from Adam Grant, bestselling author, podcast host

and professor at The Wharton School. In fact, this question of his is
such a hit that we got multiple submissions of it from folks other
than Grant, citing him as the inspiration — likely due to the opinion
piece he penned it for The New York Times: “The culture of a
workplace — an organization’s values, norms and practices — has
a huge impact on our happiness and success,” he says. “Values are
the principles people say are important and, more crucially, the
principles people show are important through their actions.” (Look
for more of Grant's advice on how to standout as an original here on
The Review.)
Liz Fosslien, Head of Content at Humu, is also a big fan of this
question: “Grant says it’s the best way to instantly learn about the
company’s culture. In my experience, he’s absolutely right," she
says. "I’ve found people tend to either get an ‘Oh no’ look on their
face, or they light up at the memory that pops into their head. Both
reactions are strong signals about what it might be like to work
there.”

8. How have you changed during your time here?

“This is an unusual one, but it will elicit some interesting insights,”

says Camille Ricketts, Head of Marketing at Notion. “People might
talk about how they've gotten more opportunities to learn or real
mobility in their role. Sometimes they will say they've become
more resilient or stronger, which is an indication of something else,
perhaps. It gives you a fascinating perspective on what the culture
brings out in people.”

A variation of this question comes from Nikita Miller, a seasoned

product leader at Atlassian: What have you learned while working
here that you’ll take with you no matter where you go next?
Laura Del Beccaro, Co-founder and CEO, Sora

9. When you’ve done your best work here, what about the
culture has enabled you to do that?

Here’s another question, from Laura Del Beccaro, Co-founder and

CEO of Sora, that continues to test the company’s cultural fabric —
whether it supports employees like a warm, cozy blanket, or leaves
them out in the cold.
10. Has the company ever made a decision that prioritized
its values over revenue?

Most companies have a list of values — but whether those values

actually leap off the webpage and are reflected in the day-to-day
work can be a whole different story. Sean Byrnes, CEO
of Outlier, gets down to brass tacks and separates hand-waving
from harsh reality with this question.

Jiaona Zhang, VP of Product at Webflow, also wants to learn more

about the company’s values in action. “It's definitely true that most
companies have core values and that it is often hard to know what
they really mean and whether they are upheld,” she says. “To get a
better signal, I ask about the history of the core values; specially, I
ask for how the core values have been (mis)interpreted, whether
they've had to be revisited over time, and if there have been
situations where they've been weaponized.”
Liz Fosslien, Head of Content, Humu

11. How did leadership at your organization respond in

the first days of the COVID-19 crisis?

We love this topical question from Liz Fosslien of Humu,

(who previously shared her tips for leading through emotional
storms on the Review — so no surprise here that she's focused on
employees' needs). “This question can reveal a lot about a
company's culture. Did leadership put their people's safety and
well-being first? Or did they drag their feet and then double-down
on micromanaging employees?”
INTERVIEW QUESTIONS ON DIVERSITY,
EQUALITY AND INCLUSION

12. What specific initiatives has the company launched to

improve diversity and inclusion?

Another contribution from Laura Del Beccaro of Sora, this question

starts us off by looking at the concrete steps the company has taken
to create a more equitable workplace for all. While virtually every
company speaks to DEI in the form of public statements or formal
plans, it’s critical to probe and see if there’s actual weight behind it,
or simply talking points. Whether you identify as someone from an
underrepresented background in tech or not, opening up the
conversation to talk tangibles can unearth critical insights into how
the company takes care of its employees.

13. What is the title of the most senior underrepresented

person at the company?

Matt Wallaert, the behavioral scientist who we mentioned before

diving in, leaves no wiggle room for editorializing with this
question. “I focus on asking factual questions that don't have to do
with how persuasive the person can be,” he says.

14. What would 1:1's be like with my direct manager?

What types of topics would we discuss?
Howard Ekundayo, Engineering Manager, Netflix
While on its face, this might not seem to be a question specifically
about DEI, Howard Ekundayo, Engineering Manager
at Netflix, finds it can reveal how much leadership makes the effort
to include every voice and show up for employees — especially
when folks on their team can’t set aside external stressors when
they sit down at their desks in the morning. “This question can
provide insight into the degree to which a manager is inclusive,
empathetic and transparent,” he says. “Our manager's style of
leadership can significantly impact our overall success and growth
in a specific role. Given the impact of COVID-19, the heightened
coverage of systemic injustices, and anxiety stemming from the
political climate (to name a few), it's important now more than ever
that we can depend on the necessary level of support from
leadership.”

15. How do you personally learn how to be more

inclusive? What's an example of a situation in which these
learnings have changed the way you do your job?

Aubrey Blanche, Director of Equitable Design and Impact

at Culture Amp, and a self-described “Mathpath” (math nerd +
empath) is laser focused on building a more equitable future. (You
might recognize her from her previous Review interviews, where
she’s gotten incredibly concrete in outlining tactics to make your
DEI efforts less talk and more walk.) This interview question for
candidates goes beyond the bird’s eye view of the company’s
diversity and inclusion efforts as a whole, and zooms in on the
individual commitment to moving the needle on these goals.
Aubrey Blanche, Director of Equitable Design and Impact at Culture Amp,
She also dives into how the team is folding DEI principles into
everyday work with this follow-up question: How do you ensure
that your team isn’t just building for themselves and their needs?

INTERVIEW QUESTIONS ON THE EMPLOYEE

EXPERIENCE

16. Can I see your calendar for the week?

Perhaps one of the most unique questions on our list comes from
Anna Binder of Asana, but she’s got a pretty compelling argument
for why this unconventional approach could unlock a vault of
insights. “Time is your most valuable asset as a worker, and how
your team leaders spend their time will tell you what they value,”
she says.

I believe there’s truth in calendars. If

someone tells you in an interview that
they really care about the learning,
development and mentorship of their
employees, their calendar should
reflect that.
“I’ve seen a CEO who blocked off time for parent-teacher
conferences. I’ve seen a different CEO who was booked starting at
6am to 10pm every single day. When I interviewed with Asana’s
CEO, something that really stuck out to me was the time he blocked
off just for thinking and writing. He was diligent about creating the
space to do the critical reflecting and strategic work that’s necessary
to run a company effectively, for the long term.” (For another
example of calendering prowess, we recommend checking out
Front CEO Mathilde Collin’s approach.)
Anna Binder, Head of People Operations at Asana
The key to making sure this question lands, according to Binder, is
prefacing it with what you’d like to glean. “For example, you could
phrase this, ‘I’m really looking for a company that values learning
and coaching, and makes space for those opportunities. Can I see
your calendar and understand how much time you’re able to devote
to working with your reports?’” says Binder.

17. What common attributes have you found among

people who join and are successful, versus those who
aren't?
“The answers to this question give you a lens into the types of
behaviors and attitudes that are most valued — sometimes
reinforcing published company values, but other times giving you
insight into unstated norms,” says Michael Leibovich, Senior
Director of Product Marketing at AppFolio.

Cristina Cordova of Notion also hits on this same idea with her
version of this question: Can you describe someone (other than
yourself) who you think has been very successful here and share
what you believe made them successful? “Strong examples here can
often highlight opportunities for upward mobility and detail what
qualities are revered within an organization,” she says.

Another powerful way to learn which stars shine brightest and

uncover what the interviewer personally values comes courtesy of a
submission from a First Round community member: Who is the
most under-recognized person in the company, and why are they
under-recognized?

18. What are the top reasons that people have left the
company of their own volition?

While questions around employees departing can quickly be

brushed aside that they “weren’t a great fit” or “not well-equipped
for the job,” this deft phrasing from Gokul Rajaram, product leader
at DoorDash, can stir up striking conversations around clarity of
role expectations and retention.
Sean Byrnes, CEO, Outlier

19. What is something that the company changed at the

request of its employees that did not originate from an
executive?

Another one from Outlier’s Sean Byrnes, who tackles the often
broad conversation around “employee experience” by quickly
narrowing the focus to simply employee impact. How much
do employees have a voice? Is information flowing upward, or is
the company stuck in a hierarchical standstill? While particularly
valuable for folks interviewing as an individual contributor, even
managers may find this question useful to look out for their future
team’s growth potential.

INTERVIEW QUESTIONS ON FOUNDER FIT

20. Can you tell me about your founding team’s

background and why you’re tackling this particular
problem?

Ryan Hoover, Founder of Product Hunt, has a firm directive here:

More job candidates should think like

an investor.
“After all, joining a company is one of the biggest investments one
can make,” he says. Much like an investor will look closely to
assess founder/market fit and intrinsic founder motivation to
tackle this problem, so too should candidates when they’re hitching
their career goals to a startup’s wagon.

21. If I asked your investors what they're worried about,

what would they say?

Dan Pupius, Co-founder and CEO of Range, advises that you use

your likely limited time with the founding team to dive deep into
the startup’s short- and long-term prospects. To map the winding
road ahead, he also leverages this question: What milestones do you
need to hit for the next round of financing? How did you come up
with those milestones?

22. Take me through key parts of your last board deck.

How did you present the material to the board and what
were one or two key insights from the board?
Board relationships can make the seas choppy or be a startup’s life
preserver. Mike Smith, President and COO of StitchFix,
recommends this question to test the waters.

23. Who is on your speed dial for when things aren’t going
well with the business? Why that person?

Vivek Sodera, Co-founder, Superhuman

A founder’s network of advisors — whether official, like board
members, or unofficial sounding boards — can cushion some of the
bumps along any startup’s path. Who the founders trust when they
 hit a fork in the road (and why they trust them) can reveal a lot
about what they’re really looking for out of their advisors — a
cheerleader, or someone who will deliver harsh truths. This
question, from Vivek Sodera, Co-founder of Superhuman, assesses
how robust that support layer really is for leadership.

24. Can you share the details of the company’s stock

offerings for employees?

We’re folding together a cluster of questions from both Sean

Byrnes of Outlier and Dan Pupius of Range that dive into the
financial details you need to know before signing on with an early-
stage company:

 What is the last 409a valuation?

 How often do you do re-evaluations?
 Do you think there will be a secondary market for early
liquidity? Who will have access to it?
 What was the last preferred price?
 What is the total number of stock options issued and what are
the outstanding shares?
 How much of the company do investors own?
“It’s important to ask details about the company that they should be
willing to disclose to help you make a decision about whether or not
to join,” says Byrnes. “Failure to share these things is a warning
sign.”

INTERVIEW QUESTIONS ON MANAGER

COMPATIBILITY
Jiaona Zhang, VP of Product, Webflow

25. What's the hardest piece of feedback you've received,

and what's the hardest feedback you've given?

Jiaona Zhang of Webflow previously outlined her insights on the

Review for building minimum lovable products (not just MVPs)
that puts the user and their feedback at the center, and it’s still a
favorite among our readers. Zhang puts a premium not just on the
customer’s feedback — she also wants to carefully excavate how
 comfortable a future manager is with criticism on both sides of the
table. Here’s what to look for in the answer to this question:

 They’ve got a few examples on the tip of their tongue. Doling

out feedback should be a consistent line item of any people
manager’s to-do list.
 They talk about their approach. Candid, hard feedback should
never be delivered haphazardly. How did they take extra care to
create the right conditions so that this feedback could be best
received?
 Who do they typically receive feedback from? If all the
examples reference the manager receiving feedback from higher-
ups, you may have a hard time getting through if you’re trying to
signal up the chain.
26. What relative weight do you put on the way people
conduct their work, versus the work product they
generate?

Matthew Metz, (also at Ossium Health as the Director of Strategic

Partnerships) hammers home the emphasis on soft skills from a
different angle. While plenty of cultures and teams talk about
their “no brilliant jerks” policy, how is that grounded in reality?
Look for tangible examples here, and use follow-up questions to
prompt stories of when creating a psychologically safe
environment was more important than hitting a deadline.

27. How would your team describe you?

Zainab Ghadiyali, former tech and product lead at Airbnb and Facebook
“What’s your management style?” is an all-too-common question,
more likely to elicit platitudes than nuggets of wisdom — consider
this minor reframing that majorly shifts the conversation, courtesy
of Zainab Ghadiyali, a fount of career-building wisdom. She blazed
an incredible trail as a product and tech lead at Airbnb and
Facebook, and co-founded a side hustle that went on to be acquired
by Anitab.org. (She shared all of her top takeaways and advice for
forging your own curiosity-driven career path on the Review last
year and has her own newsletter where she shares writings on
product, tech and leadership.)
“One of the top three reasons people leave a job is due to manager
misfit, so during the interview it’s critical to understand what the
hiring manager’s style is,” says Ghadiyali. “Framing it from the
perspective of the reports prompts the manager to think beyond
their intent and instead consider their actual working relationships
with the team,” she says.

28. How do you cultivate and foster individual contributor

growth on the team?

Joe Blau, Sr. iOS Engineer at Uber, underlines an important point

here: Not everyone wants to (or feels ready to) lead a team. Some
folks want to be the deep-sea divers of an organization, rather than
looking down from above. Yet many companies neglect these
critical individual contributor employees, instead focusing all
development on building the skills necessary to one day step into
management’s shoes.

29. What could I have done better during the interview

process?
Kim Scott, Founder, Candor, Inc.
While not technically a question to ask during the interview, this
suggestion from Kim Scott of Radical Candor fame was too
valuable to pass up. “Here is advice I give people after they get a
job offer. Try soliciting some feedback. Does your new boss tell
you anything? You want to know if your new boss is going to give
you feedback that’s going to help you grow. If the boss says, ‘Fine,
everything was fine,’ that’s not a good sign. You already know it
was fine — you got the job. Your question is, what could you have
done better?” she says. And one final tip from Scott: “Offer some
bit of feedback on what your boss-to-be could’ve done better. See
how they respond. If they get angry or defensive don’t walk away
from that job, run!”

INTERVIEW QUESTIONS ON ROLE &

RESPONSIBILITIES

30. If after 12 months I’ve failed, where did we go wrong?

Nikhyl Singhal, VP of Product, Facebook

Nikhyl Singhal, VP of Product at Facebook, most often finds this
question phrased as “What does success look like in the first year?”
But in his experience, he gets much clearer answers by eyeing
failure instead. “The top reason why a new hire is a poor fit in a
company is kind of obvious — they fail to meet the bar set for
them. This angle allows me to tie together expectations, past
failures for new hires, and the greatest strengths and weaknesses
they see within my background so far,” he says. Singhal’s got an
eye for long-term thinking — his Review article on crafting your
product team at every stage of the company journey remains a gold
standard for product leaders, and he’s even got his own
newsletter dedicated to doling out top-notch career advice.

31. What will separate someone who is good at this job

from someone who is really stellar?

Desiree Caballero, Brand Strategist at Robinhood leans on this

question for assessing mutual fit — you want to work somewhere
that values your skills as much as the company is looking for the
ideal candidate.

It’s a favorite for Kimberly Muñoz, Engineering Manager

at Slack, as well. “When I ask this, I usually get a better picture of
what the hiring manager is looking for and the perceived needs of
the organization,” Muñoz says.

32. Think back on a really great experience that you had

with the last person who previously held this role. Why
was it so great?

“This might be basic,” Jake Fleming, Lead Designer

at Labelbox, wrote to us — but we think it’s anything but. “It could
raise a red flag for the candidate if the interviewers cannot conjure
up a great past experience with someone in this particular role. It
also gives the candidate a pretty solid idea of what success looks
like in this role at this company. Finally, it helps illuminate the
company's ideal view of that particular role and how that compares
and contrasts to the candidate’s own natural abilities and
tendencies,” he says. (Of course, this one doesn’t apply when
you’re interviewing for a brand-new position.)

33. What will my first 30, 60 and 90 days look like? Do you
have an idea of the first problems you want me to help
solve?

Alphonso Morris, Lead Product Designer, Netflix

Folks usually ask something like, “What would a typical day look
like?” but you can also take the opportunity to get much more
specific and sketch out a picture of how the early days will work in
a new role and the milestones you should hit as you pick up steam.
“Everyone wants to know what they will be working on,”
says Alphonso "Fonz" Morris, Lead Product Designer for Global
Conversion at Netflix. But this particular question may give you
another critical cue: “It shows the candidate that the company has
thought really clearly about onboarding.”

34. How do you see this position evolving as the company

grows?

Ruchi Desai, Director of Operations at XCLAIM, likes that this

question packs a one-two punch: “It shows that you as the candidate
are thinking about the big picture, are ambitious and care about
more than just the immediate tasks in front of you,” she says.
“Conversely, it gives you insight into how the manager views the
position — is the team merely filling an immediate need and piling
on unwanted tasks, or is it critical to achieving the company’s
vision and mission?”

Camille Ricketts of Notion also thinks a powerful way to stand out

from the candidate pool is with this variation of the question: If I
were to succeed in this role, what would be true for the
company? “It makes it clear that you as the candidate want to
connect your work to meaningful impact and have an authentic
desire to understand what the company needs. It sends the signal
that you want to be accountable for making real things happen,” she
says.

INTERVIEW QUESTIONS ON TEAM IMPACT &

DYNAMICS

35. Talk me through a project that initially went off the

rails that you are really proud of.
Carly Leahy, Co-founder and CCO, Modern Fertility
Carly Leahy, Co-founder and CCO of Modern Fertility, knows full
well that some of the biggest company game-changers started off on
shaky ground. But with the right team in place, it doesn’t have to
mean the project is destined for the trash bin. “I love seeing how
people can be flexible and nimble and make lemonade out of
lemons,” she says.

Carl Narcisse, former Senior Technical Recruiter at Slack, also

wishes more candidates would ask about the missteps — they often
tell you a lot more than the times everything went smoothly. He
emphasizes how the team extracted learnings with his version of
this question: What’s one project in the past year that hasn’t gone as
planned? What were the challenge areas, and how did the team
learn from that?

36. Could you tell me about a time when a co-worker went

out of their way to do something nice for a teammate?

It’s unlikely that anyone on your interview panel will come out and
state frankly that the team culture could use some work. This
question, from Kevin Deggelman, Senior Software Engineer for
the San Francisco Giants and former head of product and
engineering here at First Round, gets to the heart of what makes
teamwork shine — it’s not necessarily planning fun offsite events
or eating lunch together everyday, it’s being kind to one another.
“This is a great question to assess the culture of the prospective
team. During the interview process the company is trying to figure
out what kind of teammate you'll be, but it's often hard for yourself
as the candidate to assess what kind of team you’ll be joining,” he
says.
Lindsey O'Niell, Director of Product of Crossbeam
Lindsey O'Niell, Director of Product of Crossbeam, still remembers
when she found herself on the receiving end of this question in a
hiring process. “I had a candidate ask me what the last nice or
helpful thing I did for a coworker was. It completely took me by
surprise and I thought it was a unique way to get a sense of the
culture at a company and showed how thoughtful the candidate was
about being a supportive teammate.”

37. How does the team deal with two urgent projects with
conflicting deadlines?
“This is especially important for candidates interviewing for
leadership roles, because resource and time constraints are common
in startups,” says Todd Sundsted, CTO of Odeko. “The answers,
and how the interviewer backs it up with experience, help me
understand their tactics for balancing conflicting demands. I want to
understand how they weigh these priorities or when they push back.
It's almost always an equal-parts entertaining and valuable
conversation.”

38. Who owns the goals and how are decisions made about
what work needs to be done? What influence do I have
towards the goals set for the department?
Raven Jackson-Stone, Product Manager, Root Insurance
At its core, delivering impact as an employee involves hitting your
goals. But you also want to make sure that you have a seat at the
table when those goals get drawn up in the first place. This
question, from Raven Jackson-Stone, Product Manager at Root
Insurance, gauges the level of influence that each employee has on
the team — look out for answers that seem to indicate all OKRs
come from the top-down, with no input from those that actually
execute the directives.
39. In what ways could the team that I'm joining improve
to be more impactful and deliver more value for the
business, its stakeholders and its users?

“Ideally, the team you may join needs someone of your skill-set,
background, experience and unique contributions. With that said,
not all managers or leaders have done the work to identify where
their team is weak,” says Howard Ekundayo
(Netflix). “Additionally, the manager may not have the
organizational decision-making power to make targeted hiring
decisions even if they did do this work. The context around this
question may significantly impact your decision to join the
company, organization and team overall.”

40. How long did decision-making take with the most

recent large decision?

Anna Binder (Asana) leans on this question to gauge speed and

organizational effectiveness — but with a caveat here. “Speed is of
course really important to being a nimble organization. Four weeks
is probably too long for launching an A/B testing experiment. That
being said, you also want to look out for chaos and lack of a fine-
tuned strategy — if they launched a new product in two weeks, that
could be a red flag, too.”

Jiaona Zhang of Webflow also wants to understand scenarios where

the leadership team has disagreed and committed. “It’s really telling
when you hear about a decision and what happened after the fact —
I often learn that teams think they’ve disagreed and committed,
when in reality, they never fully committed,” she says. “It leads to
side-conversations amongst the team that can fester into churn-
inducing behavior.”

Cover photo by Getty Images / Mohd Hafiez Mohd Razali / EyeEm.